(Pyrimidin-5-yl)boronic acid → (2RS,4R)-5',5'-difluoro-2-phenyl-6-(pyrimidin-5-yl)-5',6'-dihydrospiro[chroman-4,4'-[1,3]oxazin]-2'-amine
Reaction equation
Br[C:2]1[CH:3]=[C:4]2[C@@:11]3([C:16]([F:18])([F:17])[CH2:15][O:14][C:13]([NH2:19])=[N:12]3)[CH2:10][CH:9]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:8][C:5]2=[CH:6][CH:7]=1.[N:26]1[CH:31]=[C:30](B(O)O)[CH:29]=[N:28][CH:27]=1>>[F:17][C:16]1([F:18])[CH2:15][O:14][C:13]([NH2:19])=[N:12][C@@:11]21[C:4]1[C:5](=[CH:6][CH:7]=[C:2]([C:30]3[CH:31]=[N:26][CH:27]=[N:28][CH:29]=3)[CH:3]=1)[O:8][CH:9]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:10]2Participants
3
Procedure
In a manner analogous to that described in Example 19, the cross coupling reaction of (2RS,4R)-6-bromo-5′,5′-difluoro-2-phenyl-5′,6′-dihydrospiro[chroman-4,4′-[1,3]oxazin]-2′-amine (intermediate B6.3) with pyrimidin-5-ylboronic acid yielded the title compound (22% yield) as a white solid. MS (ISP): m/z=409.3 [M+H]+.